1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[4-(6-Chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinyl]-1-(4-pyridyl)-4-piperidinecarboxamide

HRID 2086291Notes

Reaction equation

HRID 2086291 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:37][N:38]1[CH2:43][CH2:42][N:41]([S:44]([C:47]2[CH:56]=[CH:55][C:54]3[C:49](=[CH:50][CH:51]=[C:52]([Cl:57])[CH:53]=3)[CH:48]=2)(=[O:46])=[O:45])[CH2:40][C:39]1=[O:58]>CN(C=O)C>[Cl:57][C:52]1[CH:53]=[C:54]2[C:49](=[CH:50][CH:51]=1)[CH:48]=[C:47]([S:44]([N:41]1[CH2:42][CH2:43][N:38]([NH:37][C:13]([CH:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:12][CH2:11]3)=[O:15])[C:39](=[O:58])[CH2:40]1)(=[O:45])=[O:46])[CH:56]=[CH:55]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidHCID 227270831-Amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Product 1

HCID 22727093N-[4-(6-Chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinyl]-1-(4-pyridyl)-4-piperidinecarboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(4-pyridinyl)-4-piperidinecarboxylic acid (102 mg) and HOBt (153 mg) in DMF (25 ml) was combined with WSC (192 mg) at 0° C. and stirred at 0° C. for 1 hour. The reaction mixture was combined with 1-amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (170 mg) obtained in Example 3 and stirred at room temperature for 2 days. The reaction mixture was concentrated and the residue obtained was partitioned between dichloromethane and aqueous sodium bicarbonate, and the organic phase was washed with saturated aqueous sodium bicarbonate, dried and concentrated to obtain a residue, which was purified by a column chromatography on a basic silica gel (dichloromethane to dichloromethane: methanol=20:1) and crystallized from ethyl acetate/methanol to obtain the title compound (115 mg) as a white powder.

Workup

  1. stirringstirred at room temperature for 2 days
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue obtained
  4. customwas partitioned between dichloromethane and aqueous sodium bicarbonate
  5. washthe organic phase was washed with saturated aqueous sodium bicarbonate
  6. customdried
  7. concentrationconcentrated
  8. customto obtain a residue, which
  9. customwas purified by a column chromatography on a basic silica gel (dichloromethane to dichloromethane: methanol=20:1)
  10. customcrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-bd79d729e2aa4f688b9b54165771efa0
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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